Dimethylformamide → HCID 137329915, compound

Participants

Reaction Steps

To a solution of 4-morpholin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine (2.26 g, 5.29 mmol) in dry THF (40 mL) cooled to −78° C. was added nBuLi (2.5 M solution in hexanes, 2.75 mL, 1.3 eq.). After stirring for 20 minutes, dry N,N-dimethylformamide (617 μL, 1.5 eq.) was added, and the reaction mixture was stirred for 20 minutes at −78° C. and then warmed slowly to room temperature. After a further 30 minutes at room temperature the reaction mixture was quenched with ice/brine and then extracted exhaustively with chloroform. The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to yield compound 8 as a yellow solid (2.38 g, 99%).

Provenance & Evidence